There were so many morally challenging situations in Supernatural that even the heroes Sam, Dean, Castiel, and Jack played the role of villain at some point over the show's 15 seasons. On the flip side, the heroes were still in the wrong compared to the designated villains several times even when they were supposed to be the good guys.

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These were the times where the likes of monsters, demons, and angels, among others, either didn’t want to harm the Winchesters or had plans that didn’t carry the collateral damage the heroes did. Sam and Dean may have convinced themselves that they were doing the right thing, but they lost the moral high ground numerous times.

Jack Wanted To Bring Mary Back But The Winchesters Wanted To Kill Him

Dean shows Sam the Mal'ak box that he has been building in Supernatural

Jack lost his soul by killing Alternate Michael, which he did in order to save Sam and Dean. This made him lose his empathy while turning him into the season’s villain as he accidentally killed Mary when she pushed him too far. 

He tried to do the right thing even then, as Jack attempted to bring Mary back to life to make up for his mistake. On the other hand, the Winchesters didn’t acknowledge Jack’s remorse. Instead, they attempted to firstly lock Jack forever in the Ma’lak box and then kill him rather than understand his problem as Jack had once done for them.

Jane Only Wanted To Live But Castiel Killed Her For His Own Needs

Jane the Nephilim attacks Castiel

Jane was a Nephilim whom the show attempted to play off as a villain simply because she was an obstacle to Castiel’s mission. Castiel was fooled by Metatron to complete a spell that would seal Heaven and all the angels in it but needed the heart of a Nephilim.

Jane had done no harm to Castiel, who agreed with Metatron that she was “an abomination” simply for being the child of an angel. Jane even tried to convince Castiel to let her go but the latter eventually cut her heart out. Morally speaking, Castiel killed someone for his own needs while the designated villain was just defending herself.

Rowena Didn't Want To Have Oskar's Blood On Her Hands But Was Forced By Castiel

Rowena hugs Oskar in Supernatural

Rowena was the main villain of Season 10 and the show made it seem as if putting her in an emotionally painful situation was morally justified. In this instance, she was captured by Castiel and Sam, and forced to make a spell that would remove the Mark of Cain from Dean.

The death of someone she loved was necessary, so Crowley kidnapped Oskar, a man Rowena had loved like a son. Rowena was then forced to kill Oskar under threat by Castiel. Years later, in Season 12, Rowena reminded Crowley that she still mourned Oskar’s death and how the heroes forced her to kill someone she loved.

Amara Wanted To Change Chuck's Mind But The Winchesters Wanted To Kill Them Both

Dean talks to Amara in a diner in Supernatural

In the last season, the Winchesters came up with a plan to manipulate Amara into believing they wanted her help to trap Chuck. In reality, they planned on killing both of them in order to maintain the balance of nature, although Amara had stopped being a villain by this point.

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She even tried to save Chuck’s life at the time by attempting to convince him to change his plan to destroy the world. In return for Amara’s help and good intentions, the Winchesters only had her death in mind.

When Crowley Wanted To Help Sam But He Betrayed Him

Sam attacks Crowley

As part of his deal to make Rowena decipher the Book of the Damned, Sam agreed to kill her son Crowley. Although Crowley was still a villain, he had begun to trust Sam since the latter had made use of his help several times before.

Sam decided to betray Crowley by planting Rowena’s hex bag on him to kickstart a slow death for the King of Hell. Crowley even confessed that he had tried to become better by toning down his evil ways and Sam stabbing him in the back was a low move. Moreover, after Crowley recovered and was in a position to kill Sam, he proved to be the bigger man by letting Sam go.

When The Winchesters Bound Death To Kill Castiel Who Had Let Them Live

A beat-up Castiel stares at Death with Dean watching in background in Supernatural

At a time when fans wanted more “Destiel” shipping moments, the show decided to turn Castiel into a villain in Season 7. Still, he let Sam and Dean go despite being in a position to end them with just a snap as Castiel claimed he was honoring their prior friendship.

Rather than give Castiel the same benefit, the Winchesters bound Death himself and ordered him to kill Castiel. In this instance, the villain had decided to spare the heroes who responded by using the first chance they got to kill him, with the Winchesters’ moral failing coming from the fact that they didn’t even try to change their friend’s corrupted mind.

Dean Killing The Phoenix Simply For Being A Monster While He Didn't Want To Fight

The Phoenix with a gun in Supernatural

Elias Finch was a Phoenix in the Old West who made sure not to hurt anyone and married a woman to have a quiet life. However, she was killed by a corrupted deputy, yet Dean had no sympathy toward Elias. Instead, he outright told him that he was evil simply because he was a monster by species.

Dean then killed Elias, complete with cheesy one-liner. From Elias’ perspective, his wife was slain despite her innocence and he was killed by Dean when he wanted nothing to do with him.

Cain's Warning That The Mark Will Corrupt But Dean Takes It Anyway

Cain fights Dean in Supernatural

Cain is presented as a terrifying Knight of Hell and plays the role of the villain once the Mark of Cain corrupts him completely. This was the fault of Dean, though, as Cain had exiled himself until Dean arrived to ask him for the Mark so he could kill Abaddon.

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Cain had even attempted to talk Dean out of it since carrying the Mark would change Dean as well, but the latter had no care for the consequences. Cain was then corrupted after this event reignited his killer instinct, with Dean then killing him after Cain’s prediction of Dean becoming bloodlusted did indeed come to pass.

When Sam Convinced Dean Not To Banish Himself And Release The Darkness Instead

Sam and Dean release the Darkness after getting rid of the Mark of Cain in Supernatural

Under the Mark of Cain’s influence, Dean became the villain of Season 10 as his bloodthirsty ways got out of hand. He still had one morally sound idea of getting banished into another realm by Death so he wouldn’t harm anyone.

Rather than understand that this was the right thing to do, Sam convinced Dean not to go through with it, resulting in Dean killing Death, and the Darkness getting released once the Mark was removed. Essentially, Sam doomed the world in favor of curing Dean, who had been content with being banished to save lives.

Dean Wanting Sam To Kill Possessed People Instead Of Exorcising Demons

Dean after punching Sam

Sam’s need to help people was one of his notable traits, but to do so he had to drink demon blood to empower himself, which ultimately corrupted him in Season 4. Dean was angered by this and claimed Sam was doing the wrong thing.

Sam argued that he was ensuring possessed people lived through his powers rather than using the demon-killing knife that ended the host as well. Despite knowing that Sam was actually living up to the family’s “saving people” motto, Dean had no care for the lives of innocent possessed victims and forced Sam to kill them if it meant killing the demon rather than use his powers.

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